That’s a very good question. First of all, Jesus said in Matthew 5:42, Give to him that asks you and from him who wants to borrow do not turn away. Now that is not intended by the Lord to be a carte blanche statement that anybody who asks you for anything you’re to give it to him.
If someone should come up and say, "I want your car, I want your home, I want your children"—you obviously can’t give those things. As a principle, I think Christ is saying that we should give when we can. What if you see someone who is sitting in front of a liquor store and they’re asking you for $5? You don’t want to help a person destroy themselves.
It’s never a Christian thing to support somebody in prodigal self-destructive behavior. The loving thing to do is not to give at that point. The same way a parent would not give a child bullets when they’re playing with a gun. But, if you don’t know, you can’t always assume the worst about people and say “I’m not going to give because they might not use this money correctly”. But it is a difficult call because people often "color" their request in ways that don't appear to support sinful and disobedient behavior. Herein lies the difficulty and the need for prayer.
What I have done on several occasions, and it has produced some interesting results. When people come up to me and ask “Can you spare some change, I’m hungry? I want to get something to eat.” I think it wise to connect them to appropriate resources. This can mean you offer to take them to buy food or gas, etc. If someone says to me, "My car is broken down and I need gas." I’ll say “Let’s go get gas together.” If they say, “Just give me the money.” I answer, “No, we don’t operate that way”.
People experiencing homelessness and poverty are in need of a loving community. There is scriptural basis for this in the story in Acts where Peter and John heal the lame man. The men respond to the beggar's request for funds not by giving him money but by giving him a better gift: the gift of healing.
People need permanent help in becoming strong. They need a connection with Jesus Christ and a faith community.
Giving cash to someone in need can be the least helpful and most temporary solution. When someone approaches me and asks for funds to get a place to stay, I think it wise to connect them with resources, introduce them to a shelter and/or refer them to an appropriate Christian counselor. I also work to get them enrolled in a program, such as our Christian Aid Center, that will provide not only a roof over their head but also, a life-transforming experience.
Everyone asking for a handout is an immeasurably precious person made in the image of God whom I am called to love...even the least of these...but a quick donation is, at best, cheap love. I believe that we must give in ways that truly liberate, empower, and transform. We must make loving, helpful connections.
The Christian community should be one that loves the whole person the way Jesus did and operates holistic community programs (or connected with them) that combine evangelism and a full range of social programs. We can then direct or take the person to these centers to get groceries if necessary and—more importantly—to find help for deeper socioeconomic problems. There, staff can gently, appropriately share the love of Christ and invite the person to come to church, where Christians throw their arms around hurting persons as God transforms them for a lifetime.
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